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Lookstein started first grade at the Ramaz School in 1937, the year it was established by his father, Rabbi Joseph Lookstein, who was then senior rabbi of Congregation Kehilath Jeshurun. The school was named in honor of Joseph Lookstein's grandfather-in-law and predecessor in the pulpit, Rabbi Moses Zevulun Margolies.[2]

As a child in the 1940s and 1950s, Lookstein would maintain a "shul scorecard", tracking the weather, the subject of his father's sermon, the details of any special occasions, and the number of congregants in attendance, which hovered in the 200s, depending on the subject of the sermon.[2]

In 1958, Rabbi Lookstein began serving as Assistant Rabbi of Congregation Kehilath Jeshurun.[5] In 1966, The New York Times devoted an article to Lookstein's May 14th sermon on the weekly Torah portion of Behar / Bechukotai, in which Lookstein described the Talmud as a model for a modern civil rights manual. In the sermon, he characterized the 25th chapter of the Book of Leviticus, which is read at the beginning of Parashat Behar, as "one of the most profound sources" for the social consciousness of religion during the Civil Rights era, and went on to explicate the relevance of the Talmud, noting, for example, that it holds that no man is free if he does not have economic opportunity or the right to live where he chooses.[6][7]

Also in 1966, Lookstein began his tenure as principal of the Ramaz School.

Rabbi Lookstein's political activism began with repeated visits to the former Soviet Union, and numerous rallies on behalf of Natan Sharansky and Soviet Jewry, and it continued with activism on behalf of the Jews of Israel and worldwide.

Following the death of his father, in July 1979, Rabbi Lookstein assumed the position of senior rabbi of Congregation Kehilath Jeshurun.[8] Filled with concern at the responsibility of filling the role served by his father as the congregation's leader, he was reassured after his father's funeral by his mother, who said: "Haskel, you'll sit there; that was dad's seat", and shortly thereafter: "Well, you'll finally have a nice office"; successfully assuaging his worries.[2]

He was selected by Newsweek magazine as the most influential Orthodox pulpit rabbi in the United States in 2008, ranked second nationwide behind Conservative Rabbi David Wolpe of Los Angeles. Newsweek's rankings were based on success in congregational growth and inspiration, leadership in the community and within his denominational movement, and the ability to serve the spiritual needs of his congregation.[9]

Lookstein has a vision of an open and centrist Orthodox Judaism[10] which he defines as "a middle of the road philosophy of Orthodox Judaism that embraces the entire community",[11] with "an uncompromising love of all Jews".[12]

On January 21, 2009, Rabbi Lookstein was one of three rabbinical participants in the National Prayer Service at the National Cathedral, representing, loosely speaking, the Orthodox Jewish contingent. The Rabbinical Council of America (RCA), the primary American modern-Orthodox rabbinic association, initially took exception to his presence, stating that, "participation in a prayer service held in the sanctuary of a church is prohibited", and adding: "Any member of the RCA who attends such a service does so in contravention of this policy and should not be perceived as representing the organization in any capacity."[13] After its initial statement was publicized, however, the RCA subsequently softened its stance. Rabbi Basil Herring, its executive director, issued a new statement, saying simply: "Rabbi Lookstein did not represent the Rabbinical Council of America in attending that service, and therefore, we have no comment on the matter."[14]

A woman who was converted to Judaism by Lookstein was refused recognition as a Jew by an Israeli Rabbinical Court in Petah Tikva, Israel, part of an international controversy over just who outside of the official Israeli Rabbinate will have their conversions recognized in Israel.[15][16] The controversy gained a significantly higher profile because Lookstein also converted Ivanka Trump, daughter of Donald Trump, prior to her 2009 marriage to Jared Kushner.[17] It seemed that officials of the Israeli government, which "has traditionally not accepted conversions done in liberal streams of Judaism",[15][16] were indirectly casting aspersion on Ivanka Trump's conversion. The rejection of conversions performed by Lookstein was condemned by the Jewish Agency for Israel, the large international NGO "responsible for the immigration ... and absorption of Jews and their families from the Diaspora into Israel".[15]

In July 2016, Lookstein accepted the invitation of Ivanka Trump, a member of his congregation, to offer the opening invocation at the 2016 Republican National Convention. After the invitation was made public, many Kehilath Jeshurun congregants as well as Ramaz alumni signed a petition requesting Lookstein to refrain from appearing at the RNC, condemning Trump's "racist, misogynistic rhetoric".[18] Lookstein, responding to the uproar, backtracked, and in an e-mail sent out to the congregants, he explained that he was withdrawing from the RNC "in the interest of bringing our community together". His prepared remarks, which Lookstein also sent out, included the following benediction: [19][20]

Almighty God: We know that we are living in very dangerous times, when all of these blessings are threatened from without, by forces of terror and unimaginable brutality, and from within, by those who sow the seeds of bigotry, hatred, and violence, putting our lives and our way of life at risk.

In the aftermath, some argued that the pressure put on Lookstein to withdraw was counterproductive, inferring, from the content of his prepared remarks, a subtle rebuke to then-nominee Trump.[21][22][23]

^Heilman, Uriel. "For first time in 100 years, outsider tapped to lead Looksteins' N.Y. shul", Jewish Telegraphic Agency, August 3, 2015. Accessed August 4, 2015. "The Orthodox synagogue on Manhattan's Upper East Side voted last week to hire as its new senior rabbi Chaim Steinmetz, who for two decades has led the Montreal congregation Tifereth Beth David Jerusalem. Rabbi Haskel Lookstein, 83, who has been at the helm of Kehilath Jeshurun since the death of his father, Rabbi Joseph Lookstein, in 1979, will become rabbi emeritus.... When Steinmetz becomes senior rabbi, Associate Rabbi Elie Weinstock will become KJ's "rabbi"; rabbinic assistant Rabbi Roy Feldman will retain his role."